Practical synthesis of pinacolborane for one-pot synthesis of unsymmetrical biaryls via aromatic C-H borylation-cross-coupling sequence

摘要

A method for practical preparation of pinacolborane from borane-diethylaniline and pinacol was newly developed. Aromatic C-H borylation of arenes with pinacolborane or bis(pinacolato)diboron catalyzed by 1/2[Ir(OMe)(COD)](2)-(4,4'-di-tert-butyl-2,2'-bipyridine) at 25 degrees C in hexane to give arylboronic esters was directly followed by cross-coupling with aromatic bromides at 60 degrees C in the presence of PdCl2(dppf) (3.0 mol %) and K3PO4 in DMF. This one-pot, two-step procedure provided a variety of unsymmetrical biaryls in high yields. (C) 2008 Elsevier Ltd. All rights reserved.